Synthesis and Characterization of 2-Pyridylsulfur Pentafluorides
Synthesis and Characterization of 2-Pyridylsulfur Pentafluorides
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DOI：
10.1002/anie.201409990
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发表时间：
2015-01-02
影响因子：
16.6
通讯作者：
Dolbier, William R., Jr.
中科院分区：
文献类型：
--
作者：
Kanishchev, Oleksandr S.;Dolbier, William R., Jr.
目前在合成目标杂环化合物期间制备SF 5取代的杂环的方法需要使用SF 5官能化的芳基或炔试剂或SF 5Cl作为SF（5）官能团的来源。本文报道了2，2-联吡啶二硫化物在KF/Cl-2/MeCN体系中的过量氧化还原反应，生成13个新的2-吡啶基硫氯四氟化合物（2-SF_4Cl-吡啶）。发现这些分子通过用氟化银（I）处理进行进一步的氯-氟交换反应，从而能够容易地获得一系列的十种新的取代的2-吡啶基硫五氟化物（2-SF 5-吡啶）。这是转化现有杂环硫官能团以制备SF 5取代的杂环的第一个简单且易于规模化的实例。
Current approaches to prepare SF5-substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5-functionalized aryl or alkyne reagents or SF5Cl as a source of the SF(5)functional group. Herein we report that excess oxidative fluorination of 2,2-dipyridyl disulfide with a KF/Cl-2/MeCNsystem leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5-pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5-substituted heterocycles.